Sodium Bicarbonate → Ethyl (2-propyl-1,3-thiazol-5-yl)acetate

Reaction equation

Br[CH:2]([CH2:8][CH:9]=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:11]([NH2:16])(=[S:15])[CH2:12][CH2:13][CH3:14].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH2:12]([C:11]1[S:15][C:8]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:9][N:16]=1)[CH2:13][CH3:14]

Participants

Procedure

A mixture of 20.6 g of ethyl 2-bromo-4-oxo-butyrate, 10.9 g of thiobutyramide and 400 ml of dichloroethane was refluxed under a nitrogen atmosphere which recycling the dehydrated condensate. The mixture was cooled and then mixed with 45 ml of a saturated sodium bicarbonate aqueous solution. The mixture was decanted and the organic phase was dried and evaporated to dryness. The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture yielded 15.4 g of ethyl 2-propyl-5-thiazole-acetate. The IR spectrum in CHCl3 showed an ester carbonyl at 1737cm-1 and C=C at 1536cm-1